Effect of conjugation with a phenylethynyl group on the fluorescent properties of water-soluble arylboronic acids

ORGN 146

Shi-Long Zheng, wang@gsu.edu1, Na Lin2, Suazette Reid1, and Binghe Wang, wang@gsu.edu1. (1) Department of Chemistry and Center for Biotechnology and Drug Discovery, Georgia State University, 33 Gilmer St., Atlanta, GA 30302-4089, (2) Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, 33 Gilmer St, Atlanta, GA 30303
Water-soluble boronic acids that showed remarkable fluorescent property changes upon sugar binding are very important building blocks and reporter units for the design and synthesis of fluorescent boronolectins (boronic acid-based lectin mimics). Recently, our lab has published several such compounds that fluoresce at below 500 nm. Aimed at discovering similar boronic acid fluorescent reporter compounds that fluoresce at a longer wavelength, we have designed and synthesized a series of analogs with increased conjugation through the incorporation of a phenylethynyl moiety into our published fluorescent boronic acids. The key reaction was a microwave-facilitated Sonogashira reaction, which gave high yields. The effect of the increased conjugation on the fluorescent properties of these boronic acids will be discussed in the presentation.

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006